tagFirst TimeThe Cherry Poppers

The Cherry Poppers


Author's Note -- This is just a story. Please don't make it out to be anything more than that. Also if you are after hot sex only, you might want to jump ahead to the end as most of the story is setup. I hope those of you who read it with an open mind and just looking for entertainment or a good story will find it. Blewwater69.


Jason Robinson stirred awake, feeling the affect of the night's drinking. He had made it through. Had survived hell night and was now a brother within Theta Chi. He amazingly remembered that his big brother, Mark Klerk, wanted to talk with him as soon as he felt up to it today. Jason rolled to a sitting position on the edge of the bed.

'Oh, fuck! My head is swimming,' he thought.

Jason staggered to his feet in his dorm room and grabbed his toiletries bag. He found the aspirin bottle he kept in his top dresser drawer, grabbed his towel, and walked across the hall into the bathroom. The first thing he had to do was take a wicked piss. His bladder ached, it was so full. He fished his flaccid cock from his gym shorts and aimed at the bowl. As he started to piss the immediate relief of pressure to his bladder was clearly pleasurable.

Next Jason popped three aspirin and then stripped down for a shower. He hoped a good hot shower along with the aspirin would have the desired affects and clear his head. He shed his t-shirt and gym shorts and climbed into the warm water of the shower. Jason was on the college swim team, making varsity as a phenomenal breaststroker and butterfly swimmer. His coach thought he had chances to set many school and even conference records.

His hands soaped his strong arms and muscular shoulders and then down his slim lower body. He definitely had a swimmer's build: broad upper chest, long arms, slim waist and long strong legs. He had big hands which also aided his swimming. His girlfriend in high school had told him more than once, big hands means big cock. She was right in his case. He didn't know if that was true generally.

He finished the shower by soaping his short blonde hair and shaving. He had a light beard and shaving in the shower had always worked well for him. Quickly finishing in the bathroom he went back to his room to dress. It was already ten thirty and he needed to meet Mark before eleven thirty since he had to be at his new job by noon. Mark had helped get him a desk job at the infirmary, registering the patients, and pulling records for the old woman doctor, Dr. Whitfield. She was retiring at the end of the year. For some reason, which seemed odd to Jason, Mark was worried about her retirement.

He grabbed his jacket as it was still cool in spring in New Jersey and headed for the frat house. It was a five minute walk across campus and around the lake that separated the frat houses from the rest of the school. He knocked on Mark's door right at eleven. He could hear a TV inside the room, so he knew Mark must be up. The sound on the TV went down and then Mark opened the door inviting him in.

"Hey, little brother," Mark greeted him, with a smile. "Feeling okay?"

"Funny! What was that Schnapps you were giving me last night?"

"Yeah. Schnapps and beer, a lethal combination," Mark said, laughing.

"It's not a good idea to kill your little brother the first night," Jason said, but laughed with him.

"I knew you could handle it," Mark offered.

"Yeah, well...it took three aspirins and a nice hot shower for me to feel half right and I have to work today," Mark stated.

"Yeah...your first day with sweet old Dr.Whitfield."

"You act like she's your grandmother or something," Jason claimed.

"Well, that's what I needed to talk with you about."

"Okay, I'm all ears but I only have about forty-five minutes," Jason said.

"We better begin then," Marks said.

Mark told Jason about the history of their frat family. He went back forty years to a guy named Douglass Caulfield. It seemed Caulfield had come from a very wealthy family in New York. Something to do with Wall Street, from what Mark remembered. Caulfield had come to Princeton and pledged early in his freshman year. Theta Chi was a new fraternity on campus then, so he was nearly one of the original brothers.

The year Doug joined Theta Chi was the same year Dr. Jennifer Whitfield had entered Princeton as the new infirmary doctor. She was a pretty lady of twenty-five then, still single, and Doug took a fancy to her when he went to get some medicine for a cold once. He noticed she had a sign up for a clerk position to help her with the bookkeeping and the student medical records. He certainly didn't need the job but took it to be close to pretty Dr. Whitfield. Quickly he learned that she already had a fiancée in the military. It was during the Vietnam War.

Dr. Whitfield remained true to her fiancée and later that year they married after he returned from the war. Caulfield was disappointed that his close proximity to Dr. Whitfield had not blossomed into a relationship but he discovered something incredibly interesting in her record keeping practices. She would put an asterisk by the birthday of each girl patient that was a virgin. He had discovered this through a process of learning about the different medicines being prescribed, it was only on women's charts, and the infirmary had thin walls. He could also tell when the asterisks were added and removed thus knowing when a girl had given up her virginity.

One particularly pretty virgin with bad monthly menstrual cramps came to the notice of Caulfield. Using his money for flowers and cards, he pursued Margaret Wilson eventually getting her to agree to a date. Caulfield was quite the charmer apparently and his money allowed him to impress women with gifts, nice dinners, and shows. He always got the front row tickets to plays and other social events. Somehow his charms allowed him to eventually bed the lovely Margaret and take her virginity. The relationship lasted only a few short months and fell apart over the summer recess.

Doug kept his job with Dr. Whitfield as a sophomore. It was only a month into his sophomore year when he began to focus on another virgin with allergies. Once again, his courting skills, money, and good looks got him a date. Polly Johnson proved to be a real challenge for Caulfield to bed. The story is not completely clear after all these years, but the belief is she used other means to please Doug, but always stopped short of allowing him intercourse. It took him till Christmas and an expensive piece of jewelry to finally get Polly to give up her cherry.

Caulfield seems to have loved the challenge of the conquest more than the prize as he again broke up with Polly during spring recess. The records indicate he found two easy targets the remainder of that year, bringing his total for the year to three and his total virgin conquests to four.

"Mark...this is interesting about our Theta Chi family history but I have to get to work soon. Why was this important to tell...?"

"Just bear with me a bit longer, Jason," Mark said.

"Okay, but you got me this job, so if I'm late it won't..."

"Dr. Whitfield still puts the asterisks on her charts," Mark announced, cutting Jason off.


"She still indicates virgins on her charts," Mark claimed.

"She does?"

"Yes. And one of our Theta Chi family members has held the job you now have for over forty years, since our great benefactor, brother Douglass Caulfield, started it way back then. We're not sure how things might change after Dr. Whitfield retires, but the real message I must tell you is this. You were chosen to carry on our tradition very carefully."

"What do you mean tradition?"

"We're a family and brotherhood of cherry poppers. We relieve women of the burden of their hymen, freeing them to enjoy life more fully," Mark said.


"It's simple really. Our family line within Theta Chi has been working at and recording the conquests of virgins for all these many years."

"You've got to be kidding?" Jason gasped.

"No, thanks to a trust fund set up by our great benefactor, Mr. Caulfield, we have relieved hundreds of women of the burden of their vaginal barriers. We are the sources of pleasure to Princeton's virgins."

"This is unbelievable! You act like you're noble knights or something," Jason said.

"We are! Or I should say we have become since the days of Mr. Caulfield."

"How can you possibly think of your efforts as noble when..."

"The rest of the story is this," Mark said.

He told Jason more about the trust fund which was created as a contest. Douglass Caulfield upon graduating had put one million dollars into trust and has added a million more every five years since. With interest the fund was currently over twenty million. Upon Caulfield's death the fund will pay out to all brothers in our family. The pay out is based on numbers of virgin conquests on a percentage basis. The top virgin killer also gets a bonus of one million dollars.

"Are you serious?" Jason asked.


"Are you telling me you have been popping cherries using Dr. Whitfield's medical records as reference to identify potential conquests?"

"I'm close to the record. I have seventeen scores. The record was set five years ago at nineteen. No one has ever broken twenty," Mark said, with a laugh.

"You've popped seventeen cherries?" Jason gasped.

"Definitely. We use Dr. Whitfield records as evidence and have recorded the results in this diary for over forty years," Mark said, reaching into a drawer of his desk and producing an old looking book.

In the book were lists of women's names on each page and dates of their lost virginity. A brother's name was at the top of the page, along with dates they were at Princeton.

"This is unbelievable," Jason exclaimed.

"I know. I felt just like you at first. I also felt, like I think you do, that we're taking outrageous advantage of these women and our employer, Dr. Whitfield."

"Right," Jason agreed.

"To my surprise, it's not like that really. We're doing most - not all, but most - of these women a favor," Mark stated.

"Oh, sure," Jason challenged sarcastically.

"You'll see for yourself if you don't break the string. Every one of our brothers in the family has participated since Doug."

"What if I break the string?" Jason asked.

"Then you and I, as your immediate big brother, are out of the contest and it ends."

"Seriously? If I refuse you get hurt?"

"Yes. It's one of the keys of the contest and one that has helped keep it going all these many years."

"Wow," Jason exclaimed. "But explain to me again how we are doing these women favors? I don't get that at all."

Mark explained his reasoning and those of his predecessors as this. All the brothers since Caulfield had been chosen for looks and athletic prowess. Meaning they were all good looking guys with strong physical builds. Everyone has been over six feet tall. The women are wined and dined using a limited expense account provided by the trust. Flowers and gifts are also arranged. The trust pays for two front row seats at several area venues of sporting events, concerts, and plays.

"I think I see where you're going. The women have the time of their lives, if however briefly for losing their virginity," Jason explained.

"Yes, but not only. It may be more than a bit cavalier to say, but by bedding these women, we bring them pleasure too. You'll find to get to seventeen popped cherries or more like I have done one must choose women receptive to losing their virginity. If you choose the most beautiful, the most religious, or the ones that want to save their virginity until they find the guy they want to marry, you'll never get beyond ten in your time here. Caulfield went on to do seven more virgins for a total of eleven. The least were two guys in the puritan early-sixties. They only got three each. Some guys in the liberal seventies got into the high teens. But, as I said, no one has broken twenty."

"Part of the problem too, is that several guys have found their perfect mates and stopped trying. That has happened about a half dozen times. We're not sure what Dr. Whitfield's retirement is going to do to the record keeping, so you may well be the last of our line. Otherwise the contest ends with the last person at the time of Douglass Caulfield death and he's in his seventies."

"This is incredible," Jason exclaimed. "Whoa...I better get going to work."

"We'll talk more later. For now just do as Dr. Whitfield instructs. I already told you what to expect from the job and about the work to be done. If you want to start thinking about the contest, just make mental note of any women that come in that receive or show asterisks on their charts," Mark stated.

"Okay," Jason said standing and saying goodbye.

It was a short walk from the frat house to the infirmary at the back of the campus near the church. Jason arrived just at noon. He had been thinking hard on the walk over about this contest and what to do. He still wasn't sure this was a moral pursuit, even if it was an interesting challenge and potentially profitable. He didn't want to break the chain though or disappoint his big brother, who had worked so hard to carry on the tradition. Mark was a senior. He would be graduating in three more months. Until then, they would share the duties at the infirmary so he still had a shot at making twenty, though an outside one. It took an average of 65 days to score a virgin over the last forty years.

Dr. Whitfield was a sweet old widow. At seventy-seven she was still agile of mind and body. She played tennis with several of the professors and could hold her own. She really looked about fifty-five, no more. Mark had introduced Jason as his replacement. Dr. Jenny, as they had come to call her, was used to the Theta Chi boys choosing their own replacements. At first she wasn't quite sure if it would always work out, but after a decade of successes, she gave in and had never been disappointed. Still sharp enough to continue working she had finally decided it was time to retire anyway. The college president, a tennis partner, had reluctantly accepted.

Dr. Jenny was impressed with the handsome boy that was to be Mark's replacement. She took him through the office procedures like she had done with about twenty previous Theta Chi brothers. She found Jason sharp and eager to learn. She could tell right away he would do just fine. It was important to her that this new employee be good because he would work for the new doctor as well. She felt if she could train him well, with Mark's help, then she would be leaving the new person with a capable assistant.

As Dr. Jenny showed Jason the way the records were stored and pulled from the files each time a patient returned, Jason noticed the small asterisks next to the birthdays on several female cards. He found himself hiding a smile as he knew already what those meant. They were about a half hour into his training and through much of the office procedures when a young lady walked in with her friend. She looked miserable and obviously had a cold. When they approached the desk, Jason asked her name as Dr. Jenny had instructed. He had her sign a registration sheet, checked her ID, and then retrieved the chart from the file. The young woman had only been in once before. She was not a virgin, Jason noticed with a smile, and was probably a junior based on her age.

Jason took the chart into Dr. Jenny in her office and then returned to the front desk. He made sure the other girl was just there for support, which she was. Jason answered the phone as Dr. Jenny came out to get her patient. The call was just about how late the infirmary was open. Jason had a few charts to file, then he was out of work for the time being. The friend of the patient watched him while he filed them. Once he sat down, he noticed her trying to read but she glanced up often, so he struck up a conversation.

"Your friend looks pretty sick," Jason said.

"She's my roommate and, yeah, she has been coughing her head off all night. She's feeling pretty miserable. I just hope I don't catch whatever she has," the girl said.

"Yeah, that wouldn't be fun from the looks of it," Jason agreed.

"You new on campus? I don't recall seeing you around," the woman asked.

"Yeah, a freshman," Jason reluctantly said.

"We've all got to be freshmen sometime," the woman stated.

Jason chuckled, "I guess that's right. I'm Jason Robinson."

"Amanda Fletcher. My friend is Molly...oh, but you probably saw her chart," Amanda said.

"Sure thing," Jason agreed, noticing the woman had a nice smile to match her cute face.

The door to the office opened and Dr. Jenny led the sickly Molly Weeks out into the reception area. Dr. Jenny was handing her a prescription for something and giving her instructions on taking care of herself. Molly thanked the Doctor between sniffles and walked out the front door with Amanda. As Amanda closed the door she yelled, "Goodbye, Jason. Maybe I'll see you around."

"Hopefully," Jason yelled back, but then wondered if that had sounded weird.

Dr. Jenny had barely started into more of his training when the door opened again and a very young looking woman entered. Her hand was over her abdomen as if she was in pain. Dr. Jenny stepped aside so Jason could do his job. He asked her name, had her sign in, and pulled her chart. As he handed it to Dr. Jenny, he noticed an asterisk on the header card for Miss Megan Harrison. Dr. Jenny asked Megan to follow her into her office.

Once the door was closed Jason resumed his seat. If he sat quietly he could make out pieces of the conversation. The voices seemed to come through a heating grate in the wall behind the desk. Jason could hear Megan describing her problem as menstrual cramps.

Jason's concentration on the conversation through the wall ended abruptly when the door opened and in walked two guys. One looked fine but the other was holding his left hand as if something was wrong. As Jason looked at it he could tell the guy had a dislocated middle finger. He got the name and other information then had them sit to await the doctor. About five minutes later, Dr. Jenny emerged with Megan. Megan had some medicine in her hand and the Doctor was telling her to call her if it didn't get better very soon. As Megan left, Jason noticed she had a nice ass.

Dr. Jenny handed him the two charts back with post-it notes attached. On the post-its were notes from her examinations. Jason knew he was to type those onto the cards inside and refile them. As he typed and read the comments, he noticed there was no change to the asterisk status on Megan's card. 'She must still be a virgin,' Jason thought. A possible potential if he wanted to go through with this wild scheme of Mark's.

The rest of the day was pretty much the same. Two more colds, one sprained ankle, and a broken front tooth from a dorm fight that had ended badly for this one guy. No more virgins, just the one. Jason walked back to the frat house to try to grab dinner and finish his talk with Mark. He was still torn over the morality of what they were doing but the thought of breaking the string for his big brother was something he couldn't bring himself to do.

He found Mark and over a spaghetti dinner they continued the discussion.

"How was your first day?" Mark asked.

"Good actually. Thanks. I think I'm going to enjoy this job. Dr. Jenny is definitely a sweet lady and it's an interesting way to meet people. I met this girl Amanda today. She was pretty cool. She's a junior though, I think," Jason said.

"Is she a virgin?" Mark queried with a big smile.

"No, or at least I don't know. It was her roommate that was sick. Her name was Molly and she's not a virgin, I can tell you that."

"Molly Weeks?"

"Yes, how did you know..."

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byBlewWater69© 10 comments/ 244590 views/ 100 favorites

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